Dear Lifehacker,
I have good, sometimes great ideas from time to time but I don't really know how to get anyone to listen. Usually I start and I can see there attention fade away after a few minutes. I don't know what I'm doing wrong, or how to keep people interested. What can I do to make my pitches more interesting and get people to actually listen to them?

Sincerely,
Pitch Imperfect

Dear PI,
Making a great pitch only requires an understanding of the person you're pitching to, a knowledge of the pros and cons of your own idea, and a lot of practice. Not one of those three things is hard to come by, but if you don't have much practice pitching well it can seem a little daunting. Pitches also vary in length depending on the situation. Generally speaking, you start by making a short pitch and then, if you do well, you'll have a chance at a longer one. First, let's go over all the things required to make a great pitch and then look at how to actually give it.

Know Your Audience

Generally speaking, you can assume a couple of things about your audience (i.e. the person or persons you're pitching to):

They're busy.

They hear a lot of ideas on a regular basis and most of them are bad (or irrelevant to them).

As a result, people who hear pitches regularly have often lost their hopefulness and optimism in regards to new ideas. They know there's a chance you'll have a good one, but they also know that chance is statistically slim. On top of that, they're busy and hearing an idea that has a good chance of being bad isn't an exciting prospect.

In many cases, you have the cards stacked against you. This upsets many people because it's intimidating and feels unfair, but it's important to sympathize. The pitch recipient wants to hear a great idea more than you might think. They love great ideas, but don't necessarily expect them. It's important to understand their position so that understanding comes across in your actual pitch. Consider what it must be like to hear bad ideas several times a day when you're worried about getting things done so you can get home to your family (or other aspects of your personal life). Imagine taking the time to hear a bad idea and realize you not only wasted your limited time but also now have to give someone bad news. Even if the pitch only lasted five minutes, there's a fairly high emotional cost with being the bearer of bad news several times a day. Nobody likes being that person because it's stressful. You wouldn't like being that person. When someone says "sure, pitch me your idea," they're willing to risk that for you. To return the favor, it's important to understand that situation and tailor your pitch accordingly. (How you actually do that is something we'll discuss a little later on.)

Aside from this general assumption, specifically who you're pitching to matters. Are you pitching to someone who can instantly write you a check and make your dreams come true, or to a lower-level executive who simply vets ideas on a regular basis? Perhaps you know the person, or even work for them. Take your relationship and their abilities into account. Clearly state what you hope to gain by making your pitch and do not ask for anything they can't provide.

Vet Your Own Idea

Everything is terrible when presented poorly. I've eaten some great food that looked like diarrhea, but only because someone made a good pitch on its behalf. Part of convincing someone to consume a reasonable facsimile of excrement is understanding the bad as well as the good. You may love your idea, but it could sound like crap to someone else because they have a lot of practice pointing out the vulnerabilities. You need to know the problems with your pitch so you're not only ready to answer critical questions as they arise but even, in some cases, address the problems in the pitch.

Consider your idea in its simplest form. Doing this will help you a lot when actually crafting your pitch, but it will also make it easier to tear apart. Make a list of every problem you can think of, and why your idea could be a failure. Also make a list of the good aspects. Go through the list of problems and address each one. Reference the items on your good list as you do. They can help you come up with good responses to the problems you proposed. You may not figure out every single issue with your idea, but you'll find most of them.

In general you'll want to keep this information to yourself unless the recipient of the pitch brings it up, but there are occasions when you'll need to address a glaringly obvious problem outright. For example, say you want to create a really amazing online calendar. You would not be the first person with this idea, but perhaps your approach offers such an incredible vision that your online calendar would become an instant success. Nevertheless, if you tell someone your idea and don't address the obvious problem of direct competition you're going to look like you didn't think things through.

When your idea in its simplest form begs an obvious question, answer it in the pitch. If it doesn't, simply be ready to answer the questions if they arise.

Practice Often

Practice may not make perfect, but you'll get a lot closer if you do it. Pitches mirror public speaking in many ways, but can be more intimidating because you have a very direct audience. People deliver good speeches through confidence in the material, and that confidence comes from practice.

Before you make any pitch, you should have a script. Perhaps you're really good at improvising, and that will most certainly help you, but you should know your material from start to finish so you could recite it in your sleep. You may not get through that pitch exactly as written, word for word, but it's important to know something effective you could say verbatim. You'll have to decide whether you can diverge from your script or not, but regardless you should know a version of your pitch that's distilled into a perfect, concise form. Even if you didn't use that version at all you'd still benefit from memorizing the most important points you need to make.

Once you've got your pitch down, practice with a friend or two. Once you've made your pitch, ask them to tell you what they understood. If they didn't get the core ideas, you need to go back to the drawing board. Also, ask your friend for feedback. Was there anything about your pitch that didn't make sense to them? Do they see any problems with the idea? You're not necessarily looking for advice on how to improve your pitch directly, but how they'd react if your idea was a real, tangible thing. People who don't regularly give constructive criticism give better feedback when you simply ask them for their reactions rather than opinions on your content and performance.

Write an Effective Teaser

Few people enjoy writing an elevator pitch, which I prefer to call a teaser. It's hard to take an ambitious, grand idea and cut it down to about three sentences. Some people even find this offensive because they think that their idea offers so much that it can't be appreciated in such a small form, but they're missing the point. Writing a good teaser isn't about cramming a huge concept into a tiny little box. Instead, it's about finding one thing that makes your idea really awesome and writing three sentences about it. If you can't do that, you shouldn't pitch your idea.

How do you find that one thing? Just think about what got you excited about your idea in the first place. In fact, whenever you come up with an idea, pay attention to what you're feeling and why. When you write down the idea down, include how you felt and what excited you. When writing a teaser, you want to pass that excitement on to anyone who hears it. You want to get them excited so they're eager to hear more. You want to keep things short so nobody feels like their time was wasted. Here's an example:

I want to make the best calendar app on the web. This may not sound like a new idea, but here's why it is: my calendar app ties in to your email, instant messaging services, and other modes of communication to detect events automatically. You'll never have to enter anything into your datebook again.

This idea raises a lot of questions and concerns (namely privacy and feasibility) but it's enough to pique a person's curiosity and sense of excitement. That's your goal. One of the best short pitches ever made came from flimmaker David Fincher for the movie Zodiac:

If you're unfamiliar, the movie Zodiac is about a real cartoonist who came very close to finding a real serial killer. It's a strange and compelling idea, made more interesting by the fact that it's true. When crafting a teaser, all you need is that spark of excitement.

Craft an Effective Pitch

By now, crafting your actual pitch should be pretty simple. You've made it through the door and someone's actually excited to hear what you have to say. All you have to do is deliver the excitement you inspired with your teaser. If you've thought through your idea, you won't have much trouble.

When you're giving an actual pitch, you may have as little as five minutes or as much as an hour depending on your situation. Either way, know how much time you'll have to talk prior to making the pitch and leave room for questions. Whenever possible, constructing a narrative will help you. If you're pitching an actual narrative for film or literature you're all set. If not, you can still benefit from including a narrative in your pitch. When you're telling a story, rather than describing a concept, it helps the listener want to know what's going to happen next. Consider this:

My calendar app will use "Technology X" to connect to instant messaging services, email, SMS, and more without much interaction from the user. A user will simply sign up on our web site, give us all their usernames and passwords—something everyone loves to do—and everything else will be taken care of for them. I plan to monetize using an ad-supported model on the free side and by providing an ad-free, feature-rich version for a monthly fee. Blah blah blah, money, blah blah, success, blah.

While a cool technology often speaks for itself to some extent, that's not a very interesting way to describe it. Adding a narrative helps:

I wake up every day to text messages, emails, and a bunch of other messages I need to answer. They're a hassle to get through, and even when I do I usually end up making plans that I have to add to my calendar. That means checking my phone, my Gmail, and my instant messages and move all that data into my datebook. I find this really frustrating and a waste of time, and I'm not even that busy. But rather than complain, I thought I'd see if I could fix the problem. That lead to the development of Technology X, which securely and privately connects to all of these services, detects when I've confirmed plans, and adds them to my calendar automatically.

This gives the listener a story with an end they want to hear and situations they can relate to. It's much hard to hear a bunch of dry information and think "I want that!" Share your situation with them, or the situation of a third party your idea could help. You want to create something that will help people and/or people will enjoy. Using a narrative demonstrates how that's possible.

Calm Your Nerves

We just discussed a lot of information and it might seem daunting, but calm your nerves. Pitching is easy with practice, but even the best pitches fail. Don't worry about that. You will have many ideas and opportunities, so if a single pitch doesn't land you will have another chance again. Love your idea, practice almost to an excess, accept that failure isn't a big deal if it happens, and you'll be just fine.